N, n-di-(n-octyl)-n-methyl-n-(3, 4-dichlorobenzyl) ammonium chloride and process for preparing the same



Patented Oct. 12, 1954 N,N-di- (n. OCTYL) N -METHYL- N (3,4 DI- CHLOTQOBENZYLMKMMONIUM CHLORIDE AND PROCESS FOR PREPARING THE SAME Louis L. Hallock, Terre Haute, Ind., assignor to Sterling Drug Inc., New York, N. Y., a corporation of Delaware No Drawing. Application June 2, 1952, Serial No. 291,299

Advantageously, this reaction is carried out by heating, approximately equimolecular proportions of the two reactants together at 40-100 C. If desired, the condensation product thus obtained can be submitted to purification procedures.

My invention is illustrated by the following example without, however, being limited thereto.

Example A mixture of 25.5 g. of N-methyl-di-n-wtyh amine and 19.5 g. of 3,4-dichlorobenzy1 chloride was heated on a steam bath for about sixteen hours. The solid reaction product thus obtained was dissolved in boiling acetone and the resulting solution was refrigerated. The solid product which separated from the chilled solution was collected on a filter and was then again recrystallized from acetone. The product thus obtained, which was N,N-di- (n-octyl) -N-methy1-N- (3,4- dichlorobenzyl) ammonium chloride, was dried at 2 100 C. at 5 mm. The product weighed 23.0 g. and melted at 118-120 C. The water solubility of the compound was below 0.25%; it was soluble in ethanol to the extent of 1%.

N,N di (n octyl) N methyl N (3,4- dichlorobenzyl) ammonium chloride was found to have high activity against bacteria and fungi, for example, Streptococcus hemolytzcus, Staphylococcus, aureus, Eberthella typhi, Mycobacterium tuberculosis, Clostridium welchz'i, Trichophyton interdz'gz'tale, Trichophyton mentagrophytes, Trz'chophyton gypscum, and Momlia albz'cans.

I claim:

1. N,N di (n octyl) N methyl N (3,4- dichlorobenzyl)ammonium chloride, having the formula 2. The process which comprises interacting N- methyl-di-n-octylamine and 3,4-dichlorobenzyl chloride.

References Cited in the file of this patent FOREIGN PATENTS Country Date Great Britain Dec. 8, 1936 Number vember 1947, vol. 36, pp. 350-358. 

1. N,N - DI - (N - OCTYL) - N - METHYL - N - (3,4DICHLOROBENZYL) AMMONIUM CHLORIDE, HAVING THE FORMULA 